Imidazoquines as Antimalarial and Antipneumocystis Agents
Peptidomimetic imidazolidin-4-one derivatives of primaquine (imidazoquines) recently displayed in vitro activity against blood schizonts of a chloroquine-resistant strain of Plasmodium falciparum. Preliminary studies with a subset of such imidazoquines showed them to both block transmission of P. be...
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Published in | Journal of medicinal chemistry Vol. 52; no. 23; pp. 7800 - 7807 |
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Main Authors | , , , , , , , , , , , , |
Format | Journal Article |
Language | English |
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American Chemical Society
10.12.2009
Amer Chemical Soc |
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Abstract | Peptidomimetic imidazolidin-4-one derivatives of primaquine (imidazoquines) recently displayed in vitro activity against blood schizonts of a chloroquine-resistant strain of Plasmodium falciparum. Preliminary studies with a subset of such imidazoquines showed them to both block transmission of P. berghei malaria from mouse to mosquito and be highly stable toward hydrolysis at physiological conditions. This prompted us to have deeper insight into the activity of imidazoquines against both Plasmodia and Pneumocystis carinii, on which primaquine is also active. Full assessment of the in vivo transmission-blocking activity of imidazoquines, in vitro tissue-schizontocidal activity on P. berghei-infected hepatocytes, and in vitro anti-P. carinii activity is now reported. All compounds were active in these biological assays, with generally lower activity than the parent drug. However, imidazoquines’ stability against both oxidative deamination and proteolytic degradation suggest that they will probably have higher oral bioavailability and lower hematotoxicity than primaquine, which might translate into higher therapeutic indexes. |
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AbstractList | Peptidomimetic imidazolidin-4-one derivatives of primaquine (imidazoquines) recently displayed in vitro activity against blood schizonts of a chloroquine-resistant strain of Plasmodium falciparum. Preliminary studies with a subset of such imidazoquines showed them to both block transmission of P. berghei malaria from mouse to mosquito and be highly stable toward hydrolysis at physiological conditions. This prompted us to have deeper insight into the activity of imidazoquines against both Plasmodia and Pneumocystis carinii, on which primaquine is also active. Full assessment of the in vivo transmission-blocking activity of imidazoquines, in vitro tissue-schizontocidal activity on P. berghei-infected hepatocytes, and in vitro anti-P. carinii activity is now reported. All compounds were active in these biological assays, with generally lower activity than the parent drug. However, imidazoquines’ stability against both oxidative deamination and proteolytic degradation suggest that they will probably have higher oral bioavailability and lower hematotoxicity than primaquine, which might translate into higher therapeutic indexes. Peptidomimetic imidazolidin-4-one derivatives of primaquine (imidazoquines) recently displayed in vitro activity against blood schizonts of a chloroquine-resistant strain of Plasmodium falciparum. Preliminary studies with a subset of such imidazoquines showed them to both block transmission of P. berghei malaria front mouse to mosquito and be highly stable toward hydrolysis at physiological conditions. This prompted Lis to have deeper insight into the activity of imidazoquines against both Plasmodia and Pneumocystis carinii, on which primaquine is also active. Full assessment of the in vivo transmission-blocking activity of imidazoquines, in vitro tissue-schizontocidal activity on P. berghei-infected hepatocytes, and in vitro anti-P. carinii activity is now reported. All compounds were active in these biological assays, with generally lower activity than the parent drug. However, imidazoquines' stability against both oxidative deamination and proteolytic degradation suggest that they will probably have higher oral bioavailability and lower hematotoxicity than primaquine, which might translate into higher therapeutic indexes. |
Author | Rosenthal, Philip J Gut, Jiri Marques, Catarina A Collins, Margaret S Mota, Maria M Vale, Nuno do Rosário, Virgílio E Gomes, Paula Prudêncio, Miguel Matos, Joana Nogueira, Fátima Cushion, Melanie T Moreira, Rui |
Author_xml | – sequence: 1 givenname: Nuno surname: Vale fullname: Vale, Nuno – sequence: 2 givenname: Miguel surname: Prudêncio fullname: Prudêncio, Miguel – sequence: 3 givenname: Catarina A surname: Marques fullname: Marques, Catarina A – sequence: 4 givenname: Margaret S surname: Collins fullname: Collins, Margaret S – sequence: 5 givenname: Jiri surname: Gut fullname: Gut, Jiri – sequence: 6 givenname: Fátima surname: Nogueira fullname: Nogueira, Fátima – sequence: 7 givenname: Joana surname: Matos fullname: Matos, Joana – sequence: 8 givenname: Philip J surname: Rosenthal fullname: Rosenthal, Philip J – sequence: 9 givenname: Melanie T surname: Cushion fullname: Cushion, Melanie T – sequence: 10 givenname: Virgílio E surname: do Rosário fullname: do Rosário, Virgílio E – sequence: 11 givenname: Maria M surname: Mota fullname: Mota, Maria M – sequence: 12 givenname: Rui surname: Moreira fullname: Moreira, Rui – sequence: 13 givenname: Paula surname: Gomes fullname: Gomes, Paula email: pgomes@fc.up.pt |
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Keywords | ANTI-PNEUMOCYSTIS-CARINII IMIDAZOLIDIN-4-ONE DERIVATIVES IN-VITRO TRANSMISSION-BLOCKING ANTIMALARIALS PLASMODIUM-FALCIPARUM 8-AMINOQUINOLINES TRAP MASS-SPECTROMETRY OPPORTUNISTIC INFECTIONS PNEUMONIA PRIMAQUINE Protozoa Antimalarial Apicomplexa Five membered ring Peptides Nitrogen heterocycle Peptidomimetic compound Quinoline derivatives Pneumocystis carinii In vitro Fungi Antiprotozoal agent Plasmodium falciparum Antifungal agent Structure activity relation Bicyclic compound Dipeptides Parasiticide Aromatic compound Fungi Imperfecti Chemical synthesis |
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Snippet | Peptidomimetic imidazolidin-4-one derivatives of primaquine (imidazoquines) recently displayed in vitro activity against blood schizonts of a... |
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SubjectTerms | Animals Antibiotics. Antiinfectious agents. Antiparasitic agents Antifungal agents Antimalarials - blood Antimalarials - chemical synthesis Antimalarials - chemistry Antimalarials - pharmacology Antiparasitic agents Biological and medical sciences Cell Line Chemical Phenomena Chemistry, Medicinal Disease Transmission, Infectious Drug Stability Female Humans Imidazoles - blood Imidazoles - chemical synthesis Imidazoles - chemistry Imidazoles - pharmacology Life Sciences & Biomedicine Liver - parasitology Medical sciences Mice Pharmacology & Pharmacy Pharmacology. Drug treatments Plasmodium falciparum - drug effects Pneumocystis carinii - drug effects Science & Technology |
Title | Imidazoquines as Antimalarial and Antipneumocystis Agents |
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